Abstract
Specific features of the reactions of bis(chloroethyl) 2-nitro- and 2-bromo-2-nitroethenylphosphonates with 1,3-cyclohexadiene were studied. It was found that the reaction with 2-nitroethenylphosphonate occurs stereoselectively and provides bis(2-chloroethyl) endo-(3-nitrobicyclo[2.2.2]oct-5-en-2-yl)phosphonate. 2-Bromo-2-nitroethenylphosphonate under the same conditions gives a mixture of the endo and exo isomers of the corresponding nitrobicyclooctenes. Enhanced tendency of adducts derived from gem-bromonitroethenyl-phosphonates for intramolecular transformations, such as dehydrohalogenation and aromatization, under the cycloaddition conditions was revealed.
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Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 7, 2005, pp. 1106–1110.
Original Russian Text Copyright © 2005 by Anisimova, Kuzhaeva, Berkova, Deiko, Berestovitskaya.
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Anisimova, N.A., Kuzhaeva, A.A., Berkova, G.A. et al. Reaction of (2-Nitro- and 2-Bromo-2-nitroethenyl)phosphonates with 1,3-Cyclohexadiene. Russ J Gen Chem 75, 1045–1049 (2005). https://doi.org/10.1007/s11176-005-0365-0
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DOI: https://doi.org/10.1007/s11176-005-0365-0